Jermaine joined Town on 28 July 2017 having been on trial in Scotland with Hibs.

Pennant started his career with Notts County. At the age of 15 he left to join Arsenal for £2 million.

He would later join Birmingham City and then Liverpool. Whilst with Liverpool he was part of the squad that finished runners-up in the 2007 Champions League. He also played for Stoke City in the 2011 FA Cup Final, losing 1-0 to Manchester City.

In recent years Jermaine has made appearances with Wigan Athletic and Bury. He has played abroad in India with Pune City and Singapore with Tampines Rovers.